Synthesis of [ ¹⁸ F]Arenes via the Copper-Mediated [ ¹⁸ F]Fluorination of Boronic Acids

Journal Article · Sat Nov 14 00:00:00 EST 2015 · Organic Letters

DOI:https://doi.org/10.1021/acs.orglett.5b02875· OSTI ID:1225990

Mossine, Andrew V. ^[1]; Brooks, Allen F. ^[1]; Makaravage, Katarina J. ^[2]; Miller, Jason M. ^[3]; Ichiishi, Naoko ^[2]; Sanford, Melanie S. ^[2]; Scott, Peter J. H. ^[4]

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1. Department of Radiology, University of Michigan Medical School, 1301 Catherine Street, Ann Arbor, Michigan 48109, United States
2. Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States
3. Department of Medicinal Chemistry, University of Michigan, 428 Church Street, Ann Arbor, Michigan 48109, United States
4. Department of Radiology, University of Michigan Medical School, 1301 Catherine Street, Ann Arbor, Michigan 48109, United States, Department of Medicinal Chemistry, University of Michigan, 428 Church Street, Ann Arbor, Michigan 48109, United States

Here, a copper-mediated radiofluorination of aryl- and vinylboronic acids with K¹⁸F is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [¹⁸F]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.

• Research Organization: Univ. of Michigan, Ann Arbor, MI (United States)
• Sponsoring Organization: USDOE Office of Science (SC)
• Grant/Contract Number: SC0012484
• OSTI ID: 1225990
• Alternate ID(s): OSTI ID: 1345033
• Journal Information: Organic Letters, Journal Name: Organic Letters Vol. 17 Journal Issue: 23; ISSN 1523-7060
• Publisher: American Chemical Society
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY